Exp188

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Objectives

  • To study the effect of concentration on the precipitation of ugi product
  • To synthesize three Ugi adducts from in methanol using Ugi 4CR following Explan005. If solid products are obtained, the experiment will serve as a template for an automated run. This experiment is a follow-up of Exp185 and Exp 187 varying the concentrations of the reagents used.

Procedure

To two one dram vials, charged with methanol (1mL), 4- (trifluoromethyl benzaldehyde (0.25mmol), respective amines (0.25mmol), methactrylic acid (0.25mmol) and t-butyl isocyanide (0.25mmol) was added in that order. After each addition, the resulting solution was vortexed for 15 seconds and confirmed that a homogeneous solution had been obtained. The vial was capped tight and left at room temperature..
Sample ID
 Aldehyde
 Amine
 Acid
 Isocyanide
 Ppt (Y/N) & Yield
188-1
 4- (trifluoromethyl) benzaldehyde
(0.25mmol-34.1uL)
 5-Methylfurfurylamine
(0.25mmol-27.8L)
 Methacrylic acid
(0.25mmol-21.2uL)
 t-butylisocyanide
(0.25mmol-28.2uL)
 N
188-2
 4- (trifluoromethyl) benzaldehyde
(0.25mmol-34.1uL)
 Benzylamine
(0.25mmol-27.3uL)
 Methacrylic acid
(0.25mmol-21.2uL)
 t-butylisocyanide
(0.25mmol-28.2uL)
 N
188-3
 4- (trifluoromethyl) benzaldehyde
(0.25mmol-34.1uL)
 t-butylamine
(0.25mmol- 26.2uL)
 Methacrylic acid
(0.25mmol-21.2uL)
 t-butylisocyanide
(0.25mmol-28.2uL)
 N

Results

Exp ID
 Day1
 Day-4
 Final
188-1
 188-1day1.JPG
 188-1day4.JPG
 No Ppt
188-2
 188-2day1.JPG
 188-2day4.JPG
 No Ppt
188-3
 188-3day1.JPG
 188-3day4.JPG
 No Ppt

Discussion

After 8 days of monitoring..no precipitate is observed. However sample 188-2 formed solid precipitate after 5 days when a higher concentration of reagents was used Exp187.

Conclusion

The conditions and reagent concentrations used is unsuitable to precipitate a ugi product for the given samples.

Log

2008-05-08

19:00 Added methanol (1mL) to three small vials labelled 188-1, 188-2 and 188-3. Then added 4- (trifluoromethyl) benzaldehyde to each vial, vortexed for 15s each. This was followed by the addition of respective amines (from the table above) to each vial, vortexed for 15s..then added methacrylic acid to each, vortexed 15s each and finally t-butyl isocyanide was added to the vials..vortexed for 15s.
20:30 Obtained pictures of the vials. (series - Day 1)

2008-05-09

10:00 Obtained pictures of the vials. (series - Day 4)

Tags

Chemical
 Inchi
 Inchikey
4- (trifluoromethyl benzaldehyde
 InChI=1/C8H5F3O/c9-8(10,11)7-3-1-6(5-12)2-4-7/h1-5H
 BEOBZEOPTQQELP-UHFFFAOYAG
5-Methylfurfurylamine
 InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3
 YSEAGSCGERFGBL-UHFFFAOYAH
Benzylamine
 InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2
 WGQKYBSKWIADBV-UHFFFAOYAL
tert-butylamine
 InChI=1/C4H11N/c1-4(2,3)5/h5H2,1-3H3
 YBRBMKDOPFTVDT-UHFFFAOYAT
Methacrylic acid
 InChI=1/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)
 CERQOIWHTDAKMF-UHFFFAOYAE
t-butyl isocyanide
 InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3
 FAGLEPBREOXSAC-UHFFFAOYAL
188-2
 InChI=1/C24H27F3N2O2/c1-16(2)22(31)29(15-17-9-7-6-8-10-17)20(21(3 ​0)28-23(3,4)5)18-11-13-19(14-12-18)24(25,26)27/h6-14,20H,1,15H2,2​ -5H3,(H,28,30)
 KPGSTEQWODPHDS-UHFFFAOYAL
188-1
 InChI=1/C23H27F3N2O3/c1-14(2)21(30)28(13-18-12-7-15(3)31-18)19(20 ​(29)27-22(4,5)6)16-8-10-17(11-9-16)23(24,25)26/h7-12,19H,1,13H2,2​ -6H3,(H,27,29)
 SAWKKHAHHFXDJA-UHFFFAOYAY
188-3
 InChI=1/C21H29F3N2O2/c1-13(2)18(28)26(20(6,7)8)16(17(27)25-19(3,4)5)14-9-11-15(12-10-14)21(22,23)24/h9-12,16H,1H2,2-8H3,(H,25,27)/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-12,10-12,11-12,12-12,13-12,14-12,15-12,16-12,17-12,18-12,19-12,20-12,21-12,22-19,23-19,24-19,25-14,26-14,27-16,28-16